Triethylamine → HCID 20499868, compound

HRID 2166608Notes

Reaction equation

HRID 2166608 reaction equation
[O:1]1[CH:6]([C:7]([OH:9])=[O:8])[CH:2]1[C:3]([OH:5])=O.[C:10]1([K])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(Cl)(=O)C(Cl)=O.Cl.CN.[CH2:26]([N:28](CC)CC)C>C(OCC)C>[CH3:26][NH:28][C:3](=[O:5])[CH:2]1[O:1][CH:6]1[C:7]([O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:8]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 6364545Methylamine hydrochlorideHCID 178524971HCID 178524971, compound

Product 1

HCID 20499868HCID 20499868, compoundYield 43.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

To a suspension of monophenyl potassium epoxysuccinate (1.23 g) in ethyl ether (30 ml), oxalyl chloride (0.7 g) in ethyl ether was added dropwise with stirring under ice-cooling and the mixture was stirred for an hour at room temperature. To the reaction mixture, a solution of methylamine hydrochloride (0.5 g) and triethylamine (1.5 g) in ethyl ether was added dropwise with stirring under ice-cooling, and the mixture was stirred for an additional hour at room temperature. The precipitate produced was filtered off and the filtrate was washed with a saturated aqueous sodium chloride solution, dried over magnesium sulfate and concentrated to dryness. The residue was purified by silica gel column chromatography using benzene as a developer to give 0.48 g of phenyl N-methyl-2,3-epoxysuccinamate (Compound No. 84) as colorless oil.

Workup

  1. additionwas added dropwise
  2. temperaturecooling
  3. stirringthe mixture was stirred for an hour at room temperature
  4. stirringwith stirring under ice-
  5. temperaturecooling
  6. stirringthe mixture was stirred for an additional hour at room temperature
  7. customThe precipitate produced
  8. filtrationwas filtered off
  9. washthe filtrate was washed with a saturated aqueous sodium chloride solution
  10. dry with materialdried over magnesium sulfate
  11. concentrationconcentrated to dryness
  12. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-988d8b4d99d24d32ab24af54ea16a927
Source dataset
uspto-grants-1983_06
Patent number
US04387238

Reaction notes

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